Nitrogenous disinfection byproducts formation and nitrogen origin exploration during chloramination of nitrogenous organic compounds

Formation of nitrogenous disinfection by-products (N-DBPs) of cyanogen chloride (CNCl), dichloroacetonitrile (DCAN) and chloropicrin was evaluated during chloramination of several selected groups of nitrogenous organic (organic-N) compounds, including alpha-amino acids, amines, dipeptides, purines, and pyrimidines, The intermediates generated, reaction pathways, and nitrogen origin in N-DBPs were explored as well. CNCl was observed in chloramination of all tested organic-N compounds, with glycine giving the highest yields. DCAN was formed during chloramination of glutamic acid, cytosine, cysteine, and tryptophan. Chloramination of most organic-N compounds except for cysteine and glutamic acid generated chloropicrin. Aldehydes and nitriles were identified as the intermediates by negative mode electrospray ionization mass spectrometry during reactions of NH(2)Cl and organic-N compounds. Labeled (15)N-monochloramine ((15)NH(2)Cl) techniques showed that nitrogen in N-DBPs may originate from both NH(2)Cl and organic-N compounds and the nitrogen partition percentages vary as functions of reactants and pH.